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Merck

I3766

Sigma-Aldrich

Isoliquiritigenin

powder

Sinónimos:

(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one, 4,2′,4′-Trihydroxychalcone

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About This Item

Fórmula empírica (notación de Hill):
C15H12O4
Número de CAS:
Peso molecular:
256.25
Beilstein/REAXYS Number:
1914296
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.77

form

powder

Quality Level

color

yellow to orange

solubility

H2O: <0.1 mg/mL
methanol: 10 mg/mL
DMSO: 20 mg/mL

storage temp.

2-8°C

SMILES string

Oc1ccc(cc1)\C=C\C(=O)c2ccc(O)cc2O

InChI

1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+

InChI key

DXDRHHKMWQZJHT-FPYGCLRLSA-N

Gene Information

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General description

Isoliquiritigenin is an aromatic ketone and belongs to the chalcone group of compound. It is derived from licorice and is a component in medicine and food.

Application

Isoliquiritigenin has been used:
  • as a bone morphogenetic protein (BMP) agonist in zebrafish embryos
  • as a guanylyl cyclase activator in zebrafish embryos
  • to test its antitumor and antiviral effects against Epstein-Barr virus-associated gastric carcinoma

Biochem/physiol Actions

Isoliquiritigenin is a soluble guanylyl cyclase activator and possesses antitumor activity. It also possesses antioxidant, antiplatelet and estrogenic properties.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Caution

Photosensitive, hygroscopic

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

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Visite la Librería de documentos

S M Yu et al.
British journal of pharmacology, 114(8), 1587-1594 (1995-04-01)
1. The vasorelaxant activity of isoliquiritigenin, isolated from Dalbergia odorifera T, was investigated in the phenylephrine-precontracted rat aorta by measuring tension, guanylate and adenylate cyclase activities, guanosine 3':5'-cyclic monophosphate (cyclic GMP) and adenosine 3':5'-cyclic monophosphate (cyclic AMP) levels. 2. Isoliquiritigenin
Small molecule modifier screen for kit-dependent functions in zebrafish embryonic melanocytes
Hultman KA, et al.
Zebrafish, 5(4), 279-287 (2008)
Suengmok Cho et al.
Biochemical and biophysical research communications, 413(4), 637-642 (2011-09-29)
Isoliquiritigenin (ILTG) is a chalcone compound and has valuable pharmacological properties such as antioxidant, anti-inflammatory, anticancer, and antiallergic activities. Recently, the anxiolytic effect of ILTG has been reported; however, its action mechanism and hypnotic activity have not yet been demonstrated.
Xuan Yuan et al.
Recent patents on anti-cancer drug discovery, 8(2), 191-199 (2012-09-12)
Isoliquiritigenin (ISL), a licorice chalconoid, is a bioactive agent with chemopreventive potential that has been patented for tumor treatment in China. This study investigated the mechanisms of ISL-induced apoptosis in ovarian carcinoma SKOV-3 cells. Cell viability was evaluated using a
Wdr68 mediates dorsal and ventral patterning events for craniofacial development
Alvarado E, et al.
PLoS ONE, 11(11), e0166984-e0166984 (2016)

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